JP5539873B2 - Improvements in or regarding organic compounds - Google Patents

Description

  The present invention relates to compositions for use in pesticides comprising certain lactamides and biologically active compounds, and methods of making and using such compositions. In particular, the present invention relates to such compositions that are formulated or contained by concentrated emulsions.

  An agrochemical (bactericidal) composition comprising dimethyllactamamide and trifolin is disclosed in DE 41 12 873 A1.

  Specific lactamides are Ratchford, WP and Fisher, CH, Journal of Organic Chemistry, 1950, 15, 317-325; Ratchford, WP, Journal of Organic Chemistry, 1950, 15, 326-332; Fein, ML and Filachione, EM, Journal of the American Chemical Society, 1953, 75, 2097-2099; and US 4,143,159.

  Currently, when developing new formulations, pharmaceutical chemists are required to address many environmental standards. Suitable solvents include the following properties: excellent solvency for pesticides or other biologically active compounds; made from plant or animal renewable resources; low skin irritation; invasive formulation ingredients such as Ideally, it exhibits the ability to reduce skin irritation associated with sodium lauryl sulfate; for example, low ecotoxicity to daphnia; low volatile organic components; and all or many of high flash points. The compositions of the present invention include a solvent that exhibits all or many of these attractive properties.

  However, all solvents are not equal in terms of their ability to dissolve biologically active compounds. The nature of the compound and its interaction with the solvent is substantially critical. It has been discovered that certain solvent classes are surprisingly effective in dissolving certain classes of biologically active compounds.

According to the invention, the following formula I:
CH ₃ CH (OH) C (═O) NR ¹ R ² (I)
{Where,
R ¹ and R ² are each independently hydrogen; C _1-6 alkyl, C _2-6 alkenyl or C _3-6 cycloalkyl [each of which is optionally phenyl, hydroxy, C _1-5 alkoxy, morpholinyl and NR ³ R ⁴ (wherein R ³ and R ⁴ are each independently, C _1-3 alkyl) is substituted by a substituent of up to 3 independently selected from; or independently from C _1-3 alkyl R ¹ and R ² together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, and optionally substituted with up to 3 substituents selected from Each optionally substituted with up to 3 substituents independently selected from C _1-3 alkyl}
And at least one biologically active compound comprising at least one aromatic 5- and / or 6-membered ring, wherein the ring comprises at least one nitrogen as a ring member A composition comprising is provided.
However,
(i) a compound of formula I is N-butoxypropyl lactamide; 1- (hydroxyethyl) piperidinyl lactamide; N-methyl-N-propyl lactamide; N- (1-ethylpropyl) lactamide; N-dimethyl lactamide; N-1,4-dimethylpentyl lactamide; N- (2-hydroxyethyl) -N-benzyl lactamide; N-morpholactolamide; N-methyl-N-butyl lactamide; When selected from the group consisting of N-isobutyl lactamide; N-allyl lactamide; N-ethyl lactamide; N-ethyl-N- (2-hydroxyethyl) lactamide; and N-isopropyl lactamide; Free of cyproconazole; and
(ii) When the compound of formula I is diethyl-lactamamide, the biologically active compound is not nicotinic acid.

  The alkyl group and the alkyl moiety are linear or branched. Examples include methyl, ethyl, iso-propyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-amyl and iso-amyl [3-methylbutyl].

  The alkenyl group and alkenyl moiety may be linear or branched and, where appropriate, may be in the (E)-or (Z) -configuration. Examples include vinyl and allyl.

  Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.

In one embodiment of the composition, in the compound of formula I, R ¹ and R ² are each independently hydrogen; or phenyl, hydroxy, C _1-5 alkoxy, morpholinyl and NR ³ R ⁴ (group R ³ and R ⁴ are each independently C _1-6 alkyl optionally substituted with up to three substituents independently selected from C _1-3 alkyl; or R ¹ And R ² together with the nitrogen atom to which they are attached form a morpholinyl ring, optionally substituted by up to 3 substituents independently selected from C _1-3 alkyl.

In an even more suitable embodiment, R ¹ and R ² are each independently hydrogen; or C _1-6 alkyl; or R ¹ and R ² together with the nitrogen atom to which they are attached form a morpholinyl ring. To do.

In a further suitable embodiment, R ¹ is methyl and R ² is methyl, propyl or butyl; or R ¹ and R ² together with the nitrogen atom to which they are attached form a morpholinyl ring. R ³ may be methyl like R ⁴ . Each optional substituent is preferably a methyl group. Suitable alkyl groups are branched; most suitable are those with a methyl group.

  The active compound in the composition may be an agrochemical.

In one embodiment of the composition, when R ² is hydrogen in the compound of formula I, R ¹ is hydrogen, methyl, ethyl, propyl, n-butyl, sec-butyl, iso-butyl, n-amyl, iso -Amyl, iso-butylenyl, n-hexyl, 1-3-dimethylbutyl, allyl, CH ₂ CH ₂ OH, 2-hydroxypropyl, 2-hydroxy-isobutyl, 1,3-dihydroxy-2-methyl-2-propyl , Tris-hydroxy-methyl-methyl, CH ₂ CH ₂ OCH ₃ , cyclohexyl, phenyl, benzyl, α-methylbenzyl, β-phenylethyl, 3-hydroxypropyl or 1-hydroxy-2-butyl;
When R ² is methyl, R ¹ is not methyl, allyl or phenyl;
When R ² is ethyl, R ¹ is not ethyl;
When R ² is n-butyl, R ¹ is not n-butyl;
When R ² is iso-butyl, R ¹ is not isobutyl;
When R ² is n-amyl, R ¹ is not n-amyl;
When R ² is iso-amyl, R ¹ is not iso-amyl;
When R ² is n-hexyl, R ¹ is not n-hexyl;
When R ² is allyl, R ¹ is not allyl;
When R ² is phenyl, R ¹ is not butyl or phenyl;
When R ² is benzyl, R ¹ is not benzyl;
When R ² is CH ₂ CH ₂ OH, R ¹ is not CH ₂ CH ₂ OH or ethyl;
When R ² is 2-hydroxypropyl, R ¹ is not 2-hydroxypropyl; and R ¹ and R ² together with the nitrogen atom to which they are attached do not form a morpholinyl, pyrrolidinyl or piperidinyl unsubstituted ring .

  The composition further comprises an aliphatic solvent; a linear or branched paraffin; a cyclic hydrocarbon; an aromatic solvent; a phosphorus-containing solvent; a sulfur-containing solvent; a nitrogen-containing solvent; an aliphatic mono-, di-, or triester; Mono- and diesters; cyclic esters; cyclic, aliphatic and aromatic ketones; alkylcyclohexanones; dialkyl ketones, acetoacetates, benzyl ketones; acetophenones; alcohols; cycloalcohols; glycols; glycol ethers And a polymer thereof; propylene glycols; glycol ether acetates; aromatic alcohols; carbonates; and a solvent selected from the group consisting of ethers and halogenated solvents.

  Particularly preferred further solvents are: white oil; decalin; mono-, di- or trialkylated benzenes; Solvesso 100 or 200ND (t); triethyl phosphonate; tributyl phosphonate; tri-2-ethylhexyl phosphonate; methyl oleate; linoleic acid; Acids; Oleic acid; Dimethyldecanoamide; Tetramethylsulfone; Dimethylsulfoxide; Alkylureas; Alkanolamines; Morpholines; Amides; Alkylalkanoates; Lactates and acetoacetates; Fumarates; Succinates; Maleates; glycerol and citrate esters; alkyl benzoates; benzylalkanoates; alkyl salicylates; phthalates and dibenzoates; γ-butyrolas Terpene fenchone; cyclohexanone; alkylcyclohexanones; 2-ethylhexanol and other alkyl alcohols; cyclohexanol; tetrahydrofurfuryl alcohol; ethylene and propylene glycol and polymers thereof; dipropylene glycol; Or monobutyl ether; dipropylene glycol diacetate or other glycol ether acetate, or tripropylene glycol monobutyl ether; benzyl alcohol; propylene or butylene carbonate; dimethyl isosorbide; alkoxy alkanols; diphenyl ether; chlorobenzene and chloroalkanes. .

  The biologically active compound is a 5-membered nitrogen-containing aromatic ring selected from the group consisting of pyrrole, pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole, and / or pyridine, It may contain a 6-membered nitrogen-containing aromatic ring which may be selected from the group consisting of pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,2,4-triazine and 1,3,5-triazine.

  When the compound is an agrochemical, the compound may be selected from the group consisting of insecticides, herbicides, plant growth regulators, acaricides, anti-nematodes, acaricides, plant activators and fungicides. Good.

  The insecticide may be selected from the group consisting of neonicotinoids, bisamides, benzoylureas and carbamates; herbicides are triazines and other photosystem 2 inhibitors, 2,6-dinitroanilines , ACCase inhibitors, PPO inhibitors, PPO inhibitors, synthetic auxins, sulfonylureas, bipyrylium herbicides, chloroacetanilides, triazolopyrimidines, pyrazoles and herbicidal safeners; plant growth The modulator may be selected from the group consisting of paclobutarazole and maleic hydrazide; and the fungicide may be triazolopyrimidines, pyrimidines, anilinopyrimidines, triazoles and other sterol-degrading agents. Methylation inhibitor, MAP kinase inhibitor, strobilurins, a Roh protraction deaminase inhibitor may be selected from the group consisting of pyrazoles and carboxamides.

FIG. 1 shows the structure of a particularly preferred fungicidal triazolopyrimidine that may be present in the composition of the present invention:

で表される化合物３-ジフルオロメチル-１-メチル-１Ｈ-ピラゾール-４-カルボン酸(９-イソプロピル-１,２,３,４-テトラヒドロ-１,４-メタノ-ナフタレン-５-イル)-アミドである。 Neonicotinoids may be thiamethoxam and imidiacloprid, bisamide may be linaxylpyr, benzoylurea may be chlorofluazuron, and carbamate may be pirimicarb. The triazines may be atrazine, simazine, and cyanazine; the other photosystem 2 inhibitors may be diuron, promethrin, and amethrin; 2,4-dinitroaniline may be fluazinam; Well, the ACCase inhibitor may be fluazifop-P-butyl and clodinahop propargyl, the PPO inhibitor may be butaphenacyl, and the synthetic auxins are fluroxypyr meptyl. The sulfonylureas may be nicosulfuron, synosulfur. , Imazosulfuron, primsulfuron methyl, prosulfuron and imazosulfuron, the bipyrylium herbicide may be paraquat and diquat, chloroacetanilide may be metazachlor, and triazolopyrimidines are , Chloranthram methyl, flora slam, and penox slam, the pyrazole is benzofenap, the herbicide safener may be a croquint set, and the plant growth regulators are paclobutrazol and maleic hydrazide The plant activator is acibenzolar-s-methyl; the pyrimidines may be buprimates, dimethylimole and ethylimole, the anilinopyrimidines are cyprodinil and pyrimethanil, the triazoles are Vitertanol, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flutriafol, penconazole, tebuconazole, triadimethone, triadimenol, difenoconazole, propiconazole, and hexaconazole, and other sterol derivatives The methylation inhibitors are flutriafol, imazalyl, and prochloraz, the triazolopyrimidine fungicide is shown in FIG. 1, the MAP kinase inhibitor may be fludioxonil, and strobilurins Xystrobin and picoxystrobin may be used, the adenosine deaminase inhibitor may be ethylmol, pyrazole is bixaphene, and carboxamides are boscalidoframethopyr, Penthiopyrad, tifluzamide, fluopyram and in particular Figure 2 below:

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)- Amide.

FIG. 3 shows a more preferred fungicide structure that may be present in the composition of the present invention.

  Compositions are from adjuvants, surfactants, polymers, thickeners, dyes or pigments, UV absorbers, antibacterial agents, salts, density modifiers, deodorants or odor improvers, taste preparation agents, cosolvents, and humectants. It may further contain at least one compound selected from the group consisting of: Surfactants can be nonionic (e.g., nonylphenol ethoxylate or alcohol ethoxylate), anionic (e.g., alkyl sulfates such as sodium lauryl sulfate, or sulfonates such as calcium dodecylbenzenesulfonate) or cationic (e.g., quaternary). Amine).

  The compound of formula I may be present in the composition in an amount of from 0.1 to 99% by weight of the composition, and the biologically active compound, preferably an agrochemical, is 0.1 to 75% by weight. % May be present.

  The compound of formula I may be present in the composition in an amount of 0.1 to 99% by weight of the composition. The pesticide may be present in an amount of 0.1 to 75% by weight and the solvent may be present in an amount of 0.1 to 90% by weight.

  The ratio of the compound of formula I to the pesticide to solvent varies depending on the need, but a ratio of 1: 1: 1 or near this limit is valuable for many of the desired formulations, but the limit for each component is The ratio of the two components of the formulation can be as low as 0.01: 1.

The lactamide component of the composition of the present invention is represented by the formula (III): [CH ₃ CH (OH) C (═O) OR ⁵ (III)] {wherein OR ⁵ is a leaving group}. Prepared by reacting with a compound of formula (II): [HNR ¹ R ² (II)] {wherein R ¹ and R ² are as defined above}. Also good. R ⁵ may be C _1-4 alkyl. This method produces HOR ⁵ as a by-product; the cleaner reaction avoids this by-product: the lactamide component of the composition of the present invention is lactide [3,6-dimethyl- [1,4] -dioxane-2,5 -Dione] is produced by reacting with a compound of formula (II): [HNR ¹ R ² (II)] {wherein R ¹ and R ² are as defined above}. be able to. Schematically such a reaction is shown below:

  The synthesis method is not limited to the above scheme. The scheme shows how lactide [3,6-dimethyl- [1,4] -dioxane-2,5-dione] can be converted to lactamide by reacting lactide with an amine [preferably primary or secondary amine]. The reaction can be performed under “solvent free” conditions, as will be appreciated by those skilled in the art.

In a particularly preferred embodiment of the composition according to the invention, the ratio of the compound of formula I: pesticide: solvent is 1: 1: 1 or 2: 1: 1 or 2: 1: 2 or 3: 1: 1 or 3: 1: 2 or 4.5: 1: 4.5 or 6: 1: 3, and in an even more preferred embodiment, the compound of formula I is dimethyl lactamide (DML) and the pesticide 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl) -amide shown in 2 It is.

  Particular embodiments of the composition include 5 to 95% DML, 0.5 to 50% of the compound of FIG. 2, and Solvesso 200ND, dipropylene glycol monobutyl ether, dipropylene glycol diacetate, methyl benzoate, benzoic acid 5 to 95% additional solvent selected from the group consisting of benzyl, dimethyldecanoamide, dipropylene glycol monomethyl ether and butyl benzoate.

  The compositions of the present invention may be formulated as concentrated emulsions, water or oil-in-water emulsions, microencapsulated formulations, aerosol sprays or fogging formulations and these are granular materials for dry application or water dispersible formulations Alternatively, those skilled in the art will recognize that it may be further formulated into a powder. The solution thus formed may be used directly on soils or plants, or alternatively in non-pesticidal applications.

  A particularly preferred dosage form of the composition is a concentrated emulsion.

  If the toxicity of the components of the composition other than the biologically active compound when it is an insecticide is low, depending on the nature of the pharmaceutical or cosmetically active ingredient, skin creams, lotions, sun creams, personal hygiene products and pharmaceuticals It will be particularly suitable for inclusion in formulations such as tablets, suppositories, inhalants, transdermal creams and drugs.

  The compositions of the present invention mean that these compositions are particularly useful in applications where they are less toxic and have an excellent environmental profile where minimization of contamination is desired. Examples of such applications include papermaking, water treatment, forest application, public health treatment, use in municipal pools, and application in other water fields, rivers, lakes, reservoirs or seas, and release to the atmosphere. Application in controlled or controlled, and applications where damage to the atmosphere is not desired. For example, in exterior and interior paints, coatings, varnishes, waxes, or other protective layers or opacifiers, colorants or screens; in dye pigments or inks; designed for home garden or industrial applications And the use of the disinfectant-containing composition according to the invention in soap or detergent applications for industrial, household or environmental specifications. The compositions of the present invention may be used in shampoos and may be used in household detergents and household cleaners (eg, surface cleaners). The active ingredient here may be a fungicide (probably azoxystrobin) in the case of shampoos or a fungicide in the case of detergents and cleaners.

  The present invention provides a method of making the compositions of the present invention disclosed above by mixing a compound of formula I with a biologically active compound as described above.

  The present invention provides a method for controlling agricultural pests, the method comprising applying to the pests or the surface thereof such that an effective amount of the composition described in the present invention can be present as an insecticide. To do. The pests may be fungi and the pesticides are fungicides, especially 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1 , 4-methano-naphthalen-5-yl) -amide (FIG. 2 above) or the fungicide shown in FIG.

  The present invention further provides the use of the composition of the present invention for controlling plant pests. In a particularly preferred use, the pest is a phytopathogenic fungus, the compound of formula I is dimethyl lactamide, and the pesticide has the following structure 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9 -Isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl) -amide (FIG. 2) and the composition further comprises Solvesso 200ND, dipropylene glycol monobutyl ether or di- A further solvent selected from the group consisting of propylene glycol diacetate, methyl benzoate, benzyl benzoate, dimethyldecanoamide, dipropylene glycol monomethyl ether and butyl benzoate is included.

  The compositions of the invention are particularly valuable in formulations where contact with human or animal skin or eyes is required or occurs by chance. Application to the use of shampoos or body cleaning fluids (e.g. shower gels, hand wipes or body wipes, and medical wipes) is advantageous due to the safe nature of the lactamide solvent present in the composition, It forms part of the cleaning formulation and may reduce some irritation of other ingredients, such as surfactants. Similarly, irritation caused by direct application of a pharmaceutical or veterinary composition to the skin or eye can be reduced compared to application of prior art compositions containing the same pharmaceutically active ingredient. The composition of the present invention may be used for antibacterial properties. Hand cleaners, floors, liquids that clean the kitchen, or vehicles benefit from the inherently low risk associated with the safe nature of lactamide solvents.

  The invention is illustrated by the following non-limiting examples.

Example 1
The following general method is used to measure the solubility of an insecticide sample in a solvent. A 2 ml portion of solvent is added to a 5 ml glass vial. Add the pesticide so that half the volume of the liquid is filled. The sample is shaken for 1 minute and allowed to stand for 24 hours. Add more insecticide to the dissolved sample, shake and let stand for another 24 hours. This process continues until the sample equilibrates for 3 days without the need for additional pesticides. The sample is then placed in a temperature controlled oven at 25 ° C. for 1 week and analyzed by high pressure liquid chromatography. All samples are filtered and centrifuged prior to chromatographic analysis.

  Two common solvents used in the insecticide industry are Solvesso200 and acetophenone. These have been used to produce many commercially concentrated emulsion formulations. For comparison, fludioxinyl, hexaconazole, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalene-5 The solubility of -yl) -amide (FIG. 2), promethrin, thiamethoxam and cyprodinil was compared between these two solvents and dimethyl lactamide. All of these compounds contain a 5- or 6-membered aromatic heterocycle. In each case, the solubility in dimethyl lactamide is superior to either Solvesso 200ND or acetophenone.

Example 2
The compounds chlorothalonil, tolalkoxydim and napropamide have chemical structures that do not contain aromatic heterocycles. Table 2 shows the solubility in three solvents: dimethyl lactamide, Solvesso 200ND and acetophenone. In each case, the solubility of the compound in dimethyl lactamide was lower than that in the other two solvents.

Claims (25)

Formula I:
CH ₃ CH (OH) C (═O) NR ¹ R ² (I)
{Where,
R ¹ and R ² are each independently C _1-6 alkyl, C _2-6 alkenyl or C _3-6 cycloalkyl}
And at least one biologically active compound comprising at least one aromatic 5- and / or 6-membered ring, wherein the ring contains at least one nitrogen atom as a ring member A composition in the form of an concentrated emulsion (EC). However,
(i) The compound represented by the above formula I is N-methyl-N-propyl lactamide; N- (1-ethylpropyl) lactamide; N, N-dimethyl lactamide; N-1,4-dimethylpentyllacto When selected from the group consisting of amide; N-methyl-N-butyl lactamide; N-isobutyl lactamide; N-allyl lactamide; N-ethyl lactamide; and N-isopropyl lactamide; Free of nazole; and
(ii) When the compound of formula I is diethyl-lactamamide, the biologically active compound is not nicotinic acid.   2. A compound according to claim 1 wherein the active compound is an agrochemical. In the compound represented by the formula I,
When R ² is methyl, R ¹ is not methyl or allyl;
When R ² is ethyl, R ¹ is not ethyl;
When R ² is n-butyl, R ¹ is not n-butyl;
When R ² is iso-butyl, R ¹ is not isobutyl;
When R ² is n-amyl, R ¹ is not n-amyl;
When R ² is iso-amyl, R ¹ is not iso-amyl;
When R ² is n-hexyl, R ¹ is not n-hexyl;
When R ² is allyl, R ¹ is not allyl; and R ¹ and R ² together with the nitrogen atom to which they are attached do not form a morpholinyl, pyrrolidinyl or piperidinyl unsubstituted ring. A composition according to 1.   Aliphatic solvents; linear or branched paraffins; cyclic hydrocarbons; aromatic solvents; phosphorus-containing solvents; sulfur-containing solvents; nitrogen-containing solvents; aliphatic mono-, di-, or triesters; Cyclic esters; cyclic, aliphatic and aromatic ketones; alkylcyclohexanones; dialkyl ketones, acetoacetates, benzyl ketones; acetophenones; alkyl alcohols; cycloalcohols; glycols; glycol ethers and their The composition according to any one of claims 1 to 3, further comprising a solvent selected from the group consisting of polymers; propylene glycols; glycol ether acetates; aromatic alcohols; carbonates; ethers and halogenated solvents. object. Wherein the solvent is a white oil; decalin; mono-, di-, or tri-alkylated benzenes; Application Benefits ethyl phosphate; tributyl phosphate; tri-2-ethylhexyl phosphate; methyl oleate; linoleic acid; linolenic acid; oleic acid; dimethyl deca Tetraamide sulfone; dimethyl sulfoxide; alkyl ureas; alkanolamines; morpholines; amides; alkyl alkanoates; lactates and acetoacetates; fumarates; succinates; adipates; Citrate esters; alkyl benzoates; benzyl alkanoates; alkyl salicylates; phthalates and dibenzoates; γ-butyrolactone; caprolactone; terpene fences; Non-alkylcyclohexanones; 2-ethylhexanol; cyclohexanol; tetrahydrofurfuryl alcohol; ethylene and propylene glycol and polymers thereof; dipropylene glycol; monomethyl or monobutyl ether; dipropylene glycol diacetate or tripropylene glycol monobutyl ether; The composition according to claim 4, selected from the group consisting of benzyl alcohol; propylene or butylene carbonate; dimethyl isosorbide; alkoxy alkanol; diphenyl ether; chlorobenzene and chloroalkanes.   6. The 5-membered nitrogen-containing aromatic ring is selected from the group consisting of pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole. Composition.   The 6-membered nitrogen-containing aromatic ring is selected from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,2,4-triazine and 1,3,5-triazine. The composition as described in any one of 1-6.   The active compound is selected from the group consisting of insecticides, herbicides, plant growth regulators, plant activators, acaricides, anti-nematodes, acaricides, and fungicides. A composition according to claim 1.   The insecticide is selected from the group consisting of neonicotinoids, bisamides, benzoylureas and carbamates; the herbicide is a triazine and other photosystem 2 inhibitors, 2,6-dinitroanilines, Selected from the group consisting of ACCase inhibitors, PPO inhibitors, synthetic auxins, sulfonylureas, bipyrylium herbicides, chloroacetanilides, triazolopyrimidines, pyrazoles and herbicidal safeners; Selected from the group consisting of sol and maleic hydrazide; and the fungicide is pyrimidines, anilinopyrimidines, triazoles and other sterol demethylation inhibitors, triazolopyrimidines, MAP kinase inhibitors, strobilurins , Adenosine deaminase inhibitor, pyra Selected from the group consisting Lumpur acids and carboxamides A composition according to any one of claims 8. The neonicotinoids are thiamethoxam and imidiacloprid, the bisamide is linaxylpyr, the benzoylurea is chlorofluazuron, the carbamate is pirimicarb; the triazines are atrazine, Simazine and cyanazine, the other optical system 2 inhibitors are diuron, promethrin and amethrin, 2,4-dinitroaniline is fluazinam, and the ACCase inhibitor is fluazifop-P-butyl and chlorodiamine. Zinahoppropargyl, the PPO inhibitor is butaphenacyl, the synthetic auxins are fluroxypyrmeptyl, and the sulfonylureas are nicosulfuron, sinosulfuron, imazosulfuron, primisulfuron methyl, pross Freon and imazosulfuron, the bipyrylium herbicides are paraquat and diquat, the chloroacetanilide is metazachlor, the triazolopyrimidines are chloransrammethyl, florasulam, and penoxsulam, and the pyrazole is Benzophenap, the herbicide safener is cloquintoset, the plant growth regulator is paclobutrazole and maleic hydrazide; the plant activator is acibenzolar-s-methyl Yes; the pyrimidines are bupirimate, dimethylimole and ethylimole; the anilinopyrimidines are cyprodinyl and pyrimethanil, and the triazolopyrimidine fungicide

Wherein the triazoles are vitertanol, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flutriafol, penconazole, tebuconazole, triadimethone, triadimenol, difenoconazole, propiconazole, and Hexaconazole, the other sterol demethylation inhibitor is furtriafol, imazalyl, and prochloraz, the MAP kinase inhibitor is fludioxonil, and the strobilurins are azoxystrobin and pico Xystrobin, the adenosine deaminase inhibitor is ethylmol, the pyrazole is bixaphene, and the carboxamides are boscalidoflamethopyl, penthiopyrad, Ruzamido, fluopyram, under及beauty following Figure 2:

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)- 10. A composition according to claim 9, which is an amide.   Selected from the group consisting of adjuvants, surfactants, polymers, thickeners, dyes or pigments, UV absorbers, antibacterial agents, salts, density modifiers, deodorants or odor improvers, taste modifiers, cosolvents, and humectants The composition according to claim 1, further comprising at least one compound.   12. The compound according to any of claims 1 to 11, wherein the compound of formula I is present in an amount of 0.1 to 99% by weight of the composition and the active compound is present in an amount of 0.1 to 75% by weight. The composition according to item.   The compound of formula I is present in an amount of 0.1-99% by weight of the composition, the active compound is present in an amount of 0.1-75% by weight, and the solvent is 0.1-90%. 13. Composition according to any one of claims 2 to 12, present in an amount of% by weight.   14. Composition according to any one of claims 1 to 13, wherein the ratio of compound of formula I: active compound: solvent is defined as 0.01-1: 0.01-1: 0.01-1. object.   The compound of formula I: active compound: solvent ratio is 1: 1: 1 or 2: 1: 1 or 2: 1: 2 or 3: 1: 1 or 3: 1: 2 or 4.5: 1: 15. A composition according to any one of claims 1 to 14, which is 4.5 or 6: 1: 3. R ¹ and R ² are each independently C _1-6 alkyl;
Said active compound is:
Fludioxinyl, diuron, hexaconazole, promethrin, epoxiconazole, thiamethoxam, cyprodinil, linaxypyr, amethrin, and Figure 2 below:

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl) -amide represented by the formula The composition of claim 1, wherein the composition is selected from the group consisting of: The compound of formula I is dimethyl lactamide and the active compound is (Figure 2 below:

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)- The composition according to any one of claims 1 to 16, which is an amide.   5-95% DML, 0.5-50% 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano 18. Composition according to any one of claims 1 to 17, comprising 5 to 95% of a solvent selected from the group consisting of -naphthalen-5-yl) -amide (Figure 2) and the solvent of claim 4. object. Wherein the solvent is dipropylene glycol monobutyl ether, dipropylene glycol diacetate, methyl benzoate, benzyl benzoate, dimethyl decanoate amide, selected from the group consisting of dipropylene glycol monomethyl ether and butyl benzoate, in claim 18 The composition as described.   20. A process for the preparation of a composition according to any one of claims 1 to 19, comprising mixing a compound of formula I according to claim 1 with an active compound according to claim 1.   A method for controlling agricultural pests, the method comprising applying to the surface of the pest or the pest so that an effective amount of an insecticide of the composition according to any one of claims 1 to 19 can be present.   The method according to claim 21, wherein the pest is a fungus and the active compound is a fungicide. The fungicide is shown in FIG. 2 below:

(3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl) 23. A process according to claim 21 or 22 having -amide).   Use of the composition according to any one of claims 1 to 19 for controlling plant pests. Said pest is a plant pathogenic fungus, a compound is dimethyl lactamide of formula I, has the structure in which the pesticide is represented in Figure 2, and wherein the composition, dipropylene glycol monobutyl ether or dipropylene 25. Use according to claim 24 comprising a solvent selected from the group consisting of glycol diacetate, methyl benzoate, benzyl benzoate, dimethyldecanoamide, dipropylene glycol monomethyl ether and butyl benzoate.